Green’s Dictionary of Slang

1. (orig. US) a problem, a cause of anxiety, a worry.

1929		C. Coe Hooch! 115: There’s too many headaches in that.
1939		G.B. Gilbert Country Preacher 77: The new rectory was both beautiful and expensive, but it proved to be a great headache. It was more pretentious than my salary warranted.
1946		S. Jackson Indiscreet Guide to Soho 57: The £5,000 a year executive and the smaller-income renter have plenty of headaches.
1953		D. Cusack Caddie 240: I began to have fewer headaches about money.
1969		‘Iceberg Slim’ Pimp 96: I won’t give you any headaches.
1977		W. Burrowes Riordans 93: Slurry disposal actually. It’s a fierce headache.
1985		N. Pileggi Wiseguy (2001) 122: He said I was making stuff up and that he had enough headaches without me driving him crazy.
1998		D. Hecht Skull Session 340: The Rizal thing was a major headache.
2000		Indep. 10 Jan. 17: A millenial cash hangover is still causing headaches.
2010		(con. 1973) C. Stella Johnny Porno 142: This my headache [...] I shouldn’t involve you.

2. (US) one’s husband or wife, boyfriend or girlfriend.

1933		Hecht & Fowler Great Magoo 25: That little headache of yours with the honky-tonk eyes is trouble — plenty.
1935		(con. late 1920s) L. Hughes Little Ham III ii : He never was no headache of mine, baby.

3. a problematic individual.

1953		I. Hamilton Till Human Voices Wake Us 27: Screws who are exceptionally scared of authority are a bit of a headache.
2002		C. Stella Jimmy Bench-Press 33: I’m wondering they don’t put all the fuckups, the headaches like myself, in O.C. just to keep us quiet.